The process disclosed in U.S. Pat. No. 4,492,802, issued to H. Rutzen et al. on Jan. 8, 1985, is the reaction of an epoxide compound having a terminal epoxide group with a salt of a tertiary amine using a quarternary ammonium compound as catalyst to produce the quarternary ammonium compound of the epoxide compound. The patent states the amount of quarternary ammonium compound used as catalyst as being from about 0.5 to about 10 weight percent based on the theoretical weight of the end product and the process requires the addition of this quarternary compound catalyst. The examples show preparation of the tertiary amine acid salt in situ by the reaction of 1.1 moles of the tertiary amine with 1 mole of the salt forming material (the acid), thus leaving 0.1 mole of unreacted free tertiary amine. Thus, the only mole ratio of tertiary amine to tertiary amine acid salt shown in this reference is 0.1:1 and the only catalysts described as useful are the quarternary ammonium compounds. There is no stated recognition that the tertiary amine per se could be a catalyst and there is no suggestion or disclosure of any siloxane compound.
In U.S. Pat. No. 4,421,932, issued to H. Rutzen et al. on Dec. 20, 1983, there is disclosed a process for manufacturing quarternary ammonium compounds by reacting an epoxide compound having a terminal epoxide group with a tertiary amine which is present as both the free amine and as the amine acid salt, followed by the addition of sufficient acid at the end of the reaction to convert all of the quarternary ammonium compound to the salt form. The patent states that from about 50 to about 90 mole percent, preferably about 60 to 80 mole percent, of the tertiary amine is converted to the amine acid salt form by the acid (column 2, line 17 et seq.), thus leaving from 50 to 10 mole percent remaining as the free tertiary amine. Thus, calculations show that the mole ratio of free amine to amine acid salt is from about 0.11:1 to about 1:1 and preferably from about 0.25:1 to about 0.67:1. As shown at column 2, lines 28- 30, the reference requires the presence of one epoxide equivalent, one amine equivalent and from about 0.5 to about 0.9, preferably about 0.6 to about 0.8 acid equivalent. This is a considerably higher amount of free amine than was found necessary for the production of quarternary ammonium pendant siloxane compounds by the process of this instant invention; it is to be noted that U.S. Pat. No. 4,421,932 contains no mention of any siloxane compound.
In European patent application No. 0 107 088. filed by R. D. Jerabek et al. and published on May 2, 1984, quarternary ammonium compounds were produced by reacting a monoepoxide and an amine containing an acylic moiety in the presence of an acid or water. The application contains no recognition of the need to control the ratio of amine to acid and no mention of a siloxane compound.